Halichondria panicea

Microbacterium sp. (from Halichondria panicea) Glucosylmannosyl glycerolipid 200 [84]... 

A sesquiterpene isothiocyanate, halipanicine (263) has been isolated from an Okinawan specimen of Halichondria panicea [265]. The relative stereochemistry of halipanicine (263) was established by synthesis [266] and later, a total synthesis was achieved [267]. 

It, along with methylbenzyl sulfide and one or two other sulfides, is responsible for the nauseating stench of Halichondria panicea, a marine sponge. 

Paniceins Ax, Bx, B2, B3, and C have been isolated from a marine sponge (Halichondria panicea) (cf. p. 65) and assigned structures (323)—(327).136 These... 

Bacterium Microbacterium sp., isolated from the sponge Halichondria panicea, produced four unusual cell-associated glycoglycerolipids GGL.l 341, GGL.2 342, GGL.3 343, and GGL. 4... 

One sponge species found in many coastal zones is the breadcrumb sponge (Halichondria panicea). Green to yellow crusts of the sponge creep across rocks and can cover an area of several feet. Breadcrumb sponges can be found as thin mats in the energetic surf zones, but in quiet tide pools, they form thicker masses. 

The common crust of bread sponge, Halichondria panicea, was found to contain large amounts of sulfur compounds, notably dimethyl trisulfide (171), to such an extent that the organism was considered hazardous to handle by the fishermen in the area. Samples of this species collected at other localities were found to contain trace amounts of the sulfur compounds. 

Hansen etal. (1995) exposed the marine demosponge Halichondria panicea to dissolved copper concentrations ranging from 0.45 (control) to 1000 tg L for 14 days. 

Nocardiopsis sp. (HB383) Sponge (Halichondria panicea) Nocapyrones A-D Antimicrobials Schneemann et ai, 2010a... 

Streptomyces sp. Sponge Halichondria panicea) Streptophenazines A-H Antibacterials Mitova eto/., 2008... 

Streptomyces sp. (HB202) Sponge [Halichondria Panicea) Mayamycin Cytotoxic Schneemann et al., 2010b... 

Schneemann, I., Ohlendorf B., Zinecker, H., Nagel, K., Wiese, J., and Imhoff J.F. (2010a) Nocapyrones A-D, y-pyrones from a Nocardiopsis strain isolated from the marine sponge Halichondria panicea. J. Nat. Prod., 73, 1444-1447. 

Baicalospongia bacillifera (0.35) Halichondria panicea (25.4) Chondrosia reniformis (0.2) Baicalospongia bacillifera (0.08) Baicalospongia bacillifera (0.08) Ectyoplasiaferox (3.4)... 

Halipanicine (R = NCS) Halichondria panicea Nakamura a/., 1991 R = NC, NHCHO Axinyssa aplysinoides Compagnone and Faulkner, 1995... 

Nakamura, H., Deng, S., Takamatsu, M., Kobayashi, J., Ohizumi, Y, and Hirata, Y. (1991) Structure of halipanidne, a new sesquiterpene isothiocyanate from the Okinawan sponge Halichondria panicea (Pallas). Agric. Biol Chem., 55, 581-583. 

Imbs, A.B. and Rodkina, S.A. (2004) Isolation of 2-methyl branched unsaturated very long chain fatty acids from marine sponge Halichondria panicea and identification of them by GC-MS and NMR. Chem. Phys. Lipids, 129, 173-181. 

The acetone extracts of Halichondria panicea yielded (52) five new related triprenylphenols , panicein-A, -Bi, -B2, -B3 and -C, each containing an aromatic sesquiterpenoid moiety linked to a quinol or quinone system, except for panicein-B2, which is the corresponding chromenol of panicein-B3 and probably an artifact of isolation. The structures of the paniceins are shown in Chart 14. 

Chart 14. Structures of paniceins, triprenylphenols from Halichondria panicea... 

In the sesquiterpenoid moiety the paniceins have the uncommon feature of an aromatic ring which, notably, has been encountered already in renieratene (126) and isorenieratene (127). These are arylcarotenoids found in the sponge Reniera japonica (syn. Halichondria panicea) 183, 184), which also yielded a third aromatic carotenoid renierapurpurin (130) 185). 

The biosynthetic derivation of these aromatic groups of terpenoid origin is a matter for conjecture, but it seems likely that 1,2-methyl migration occurs in a monocyclofarnesyl derivative (Chart 15) and in a p-end group of carotenoids as suggested by Ramage 154), followed by oxidation. The co-occurrence of methyl rra 5-monocyclofarnesate (62) and the paniceins in Halichondria panicea supports the intermediacy of a monocyclofarnesyl precursor for the latter (57). 

Among the Cis-sterols, 24-methylenecholesterol (164) which is widely distributed in marine organisms was found in Chalina arbuscula and Tetilla laminaris (25). Henze s spongosterol from Suheritesv/2is separated into neospongosterol (159) and cholestanol (147), (27). Cholestanol (147) was found in eleven other sponges (77), often as a major sterol constituent, and cholesterol (149) was found in Microciona prolifer a and Halichondria panicea (24). 

Methyl Tran -Monocyclofarnesate from the Sponge Halichondria panicea. Experientia 29, 1063 (1973). 

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